[2-methyl-5-(4-methylphenyl)-3-thienyl]perfluorocyclopentene | 911419-52-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: [2-methyl-5-(4-methylphenyl)-3-thienyl]perfluorocyclopentene
• 英文别名: 1-(2-methyl-5-p-methylphenylthiophen-3-yl)perfluorocyclopentene；2-methyl-3-(perfluorocyclopent-1-en-1-yl)-5-(p-tolyl)thiophene；1-[2-methyl-5-(p-methylphenyl)-3-thienyl]perfluorocyclopentene；3-(2,3,3,4,4,5,5-Heptafluorocyclopenten-1-yl)-2-methyl-5-(4-methylphenyl)thiophene；3-(2,3,3,4,4,5,5-heptafluorocyclopenten-1-yl)-2-methyl-5-(4-methylphenyl)thiophene
• CAS: 911419-52-8
• 化学式: C₁₇H₁₁F₇S
• 分子量: 380.329
• InChiKey: UTONNVMCNKMGMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-溴-2,4-二甲氧基嘧啶 、 [2-methyl-5-(4-methylphenyl)-3-thienyl]perfluorocyclopentene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以48%的产率得到1-(2,4-dimethoxy-5-pyrimidinyl)-2-[2-methyl-5-(4-methylphenyl)-3-thienyl]perfluorocyclopentene
  参考文献：
  名称：

  Photochromism of asymmetrical diarylethenes with a pyrimidine unit: Synthesis and substituent effects

  摘要：

  Five photochromic diarylethenes with a six-membered pyrimidine moiety were synthesized to investigate the effects of the substituents on their photochromic behaviors, and the structures of four of the diarylethenes were determined by single-crystal X-ray diffraction analysis. The pyrimidine moiety was connected directly to the central cyclopentene ring as an aryl moiety to participate the photoisomerization reaction in solution, solid amorphous films, and crystalline phase. All of the diarylethene derivatives showed favorable photochromism and functioned as notable fluorescent photo-switches in both solution and solid media. The electron-donating substituents enhanced their cyclization quantum yields, fatigue resistance, and fluorescence quantum yields, whereas the electron-withdrawing groups exerted inversed actions on the diarylethenes. The results revealed that the pyrimidine moiety and substituents played a very important role during the process of photoisomerization reactions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.10.047
• 作为产物：
  描述：

  4-溴-5-甲基噻吩-2-硼酸 在 四(三苯基膦)钯 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 17.83h， 生成 [2-methyl-5-(4-methylphenyl)-3-thienyl]perfluorocyclopentene
  参考文献：
  名称：

  光致变色吲唑-噻吩混联型全氟环戊烯化合物 及其合成方法和应用

  摘要：

  本发明属于化学合成领域，公开了一种光致变色吲唑‑噻吩混联型全氟环戊烯化合物及其制备方法。本发明光致变色吲唑‑噻吩混联型全氟环戊烯化合物的主要用途有：搀杂高分子材料或制成膜片，实用于超高密度、可擦写有机光子型信息存储材料；用于制备光控开关元件；用于制备光致变色发光器件等。

  公开号：

  CN104892588B

文献信息

• Synthesis and the effects of substitution upon photochromic diarylethenes bearing an isoxazole moiety
  作者：Shouzhi Pu、Hui Li、Gang Liu、Weijun Liu、Shiqiang Cui、Congbin Fan

  DOI：10.1016/j.tet.2010.12.041

  日期：2011.2

  diarylethene derivatives. As compared to the unsubstituted parent diarylethene, introduction of the electron-donating/withdrawing substituents could efficiently modulate the optical and electrochemical properties of the diarylethenes bearing an isoxazole moiety. All results indicated that the isoxazole moiety and the substitution effects played a very important role during the process of photochromic reaction

  合成了一类新的带有异恶唑部分的不对称光致变色二硫杂环丁烷，并系统地研究了取代对其的光学和电化学性能的影响。每种化合物均在溶液和聚（甲基丙烯酸甲酯）薄膜中均表现出显着的光致变色作用并充当荧光光开关。给电子的取代基有效地将最大吸收和发射峰移向更长的波长方向，而吸电子的取代基显着提高了这些二芳基乙烯衍生物的荧光量子产率和氧化开始。与未取代的母体二芳基乙烯相比，给电子/吸电子取代基的引入可以有效地调节带有异恶唑部分的二芳烃的光学和电化学性质。所有结果表明，异恶唑部分和取代作用在这些二芳基乙烯衍生物的光致变色反应过程中起着非常重要的作用。
• Photochromism of new unsymmetrical diarylethenes based on the hybrid of azaindole and thiophene moieties
  作者：Zhiyuan Sun、Hui Li、Gang Liu、Congbin Fan、Shouzhi Pu

  DOI：10.1016/j.dyepig.2014.03.003

  日期：2014.7

  A new class of photochromic diarylethenes with both azaindole and thiophene moieties were synthesized to investigate the effects of the substituents on their photochromic behaviors, and their structures were determined by single crystal X-ray diffraction analysis. The azaindole moiety was connected directly to the central cyclopentene ring as a heteroaryl moiety to participate the photoisomerization

  合成了一类新的同时具有氮杂吲哚和噻吩基团的光致变色二蒽，以研究取代基对其光致变色行为的影响，并通过单晶X射线衍射分析确定其结构。氮杂吲哚部分作为杂芳基部分直接连接到中央环戊烯环上，以参与溶液，固体无定形薄膜和单晶相中的光异构化反应。每个二芳烃在溶液和固体介质中均显示出显着的荧光光开关。给电子的取代基显着提高了其环化量子产率，而吸电子基团大大提高了其闭环异构体的摩尔吸收系数。循环伏安法研究表明，当从给电子取代基转变为吸电子取代基时，带有氮杂吲哚的二芳烃的带隙显着增加。结果表明，氮杂吲哚部分和取代基在这些二芳烃的光异构化反应过程中起着至关重要的作用。
• Fluorescence Commutation and Surface Photopatterning with Porphyrin Tetradithienylethene Switches
  作者：Thomas Biellmann、Agostino Galanti、Julien Boixel、Jennifer A. Wytko、Véronique Guerchais、Paolo Samorì、Jean Weiss

  DOI：10.1002/chem.201704222

  日期：2018.2.1

  efficiently quenched in solution. The reversible, photo‐switching of luminescence was retained in a tetra‐DTE free‐base porphyrin‐doped polystyrene film, for which photo‐patterning was demonstrated by confocal scanning microscopy. The tunable fluorescent properties of this multi‐DTE framework render this compound of interest as a photo‐rewritable fluorescent ink.

  合成并研究了四种四噻吩基乙烯（DTE）取代的卟啉，游离碱1H 2和三种金属衍生物（1Zn，1Co，1Ni）。这些二分体的DTE单元通过间-苯基间隔基连接到卟啉的内消旋位置，在所有情况下均表现出可逆的光致变色性质，通过吸收和NMR证实，转化为光平稳态（PSS）的最高可达88％光谱学。化合物 1H 2和1Zn在溶液中呈荧光色并显示红色发射。在用紫外线照射以触发DTE封闭时，溶液中游离碱和卟啉锌的荧光都非常有效地猝灭。可逆的，发光的光开关保留在四-DTE游离基卟啉掺杂的聚苯乙烯薄膜中，通过共聚焦扫描显微镜证明了其光图案化。这种多DTE框架的可调荧光特性使该化合物成为可光重写的荧光墨水。
• 光致变色吲唑-噻吩混联型全氟环戊烯化合物 及其合成方法和应用
  申请人：江西科技师范大学

  公开号：CN104892588B

  公开（公告）日：2017-07-07

  本发明属于化学合成领域，公开了一种光致变色吲唑‑噻吩混联型全氟环戊烯化合物及其制备方法。本发明光致变色吲唑‑噻吩混联型全氟环戊烯化合物的主要用途有：搀杂高分子材料或制成膜片，实用于超高密度、可擦写有机光子型信息存储材料；用于制备光控开关元件；用于制备光致变色发光器件等。
• Photochromism of asymmetrical diarylethenes with a pyrimidine unit: Synthesis and substituent effects
  作者：Hongliang Liu、Shouzhi Pu、Gang Liu、Bing Chen

  DOI：10.1016/j.dyepig.2013.10.047

  日期：2014.3

  Five photochromic diarylethenes with a six-membered pyrimidine moiety were synthesized to investigate the effects of the substituents on their photochromic behaviors, and the structures of four of the diarylethenes were determined by single-crystal X-ray diffraction analysis. The pyrimidine moiety was connected directly to the central cyclopentene ring as an aryl moiety to participate the photoisomerization reaction in solution, solid amorphous films, and crystalline phase. All of the diarylethene derivatives showed favorable photochromism and functioned as notable fluorescent photo-switches in both solution and solid media. The electron-donating substituents enhanced their cyclization quantum yields, fatigue resistance, and fluorescence quantum yields, whereas the electron-withdrawing groups exerted inversed actions on the diarylethenes. The results revealed that the pyrimidine moiety and substituents played a very important role during the process of photoisomerization reactions. (C) 2013 Elsevier Ltd. All rights reserved.